Hydrochloric Acid → 1-(4-n-Pentyloxyphenyl)acrolein

HRID 351538Notes

Reaction equation

HRID 351538 reaction equation
[CH2:1]([O:6][C:7]1[CH:18]=[CH:17][C:10]([C:11](N(C)OC)=[O:12])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:19]([Mg]Br)=[CH2:20].Cl>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([CH:19]=[CH2:20])=[O:12])=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22713252N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamineHCID 178418507HCID 178418507, compound

Product 1

HCID 227132221-(4-n-Pentyloxyphenyl)acrolein

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamine (4.52 g) in tetrahydrofuran (25 ml) was added 1.6 molar tetrahydrofuran solution of vinylmagnesium bromide (25.5 ml) at −50° C. dropwise and the mixture was stirred for 3 hours at −20° C. To the mixture was added 1N HCl (50 ml) dropwise and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate)=(8/2) to give 1-(4-n-pentyloxyphenyl)acrolein (2.40 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate)=(8/2)

Sources & evidence

ORD record
ord-54854ecbde264558a85257d58ac292dd
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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